


In Need of a Daddy

by saltyhunter



Category: Supernatural
Genre: Alternate Universe- No Supernatural, Anal Fingering, Anal Sex, Bathroom Sex, Bottom Castiel/Top Dean Winchester, Dom/sub, Light Dom/sub, M/M, Masturbation in Bathroom, Nude Photos, Office Sex, Rough Oral Sex
Language: English
Status: Completed
Published: 2018-10-23
Updated: 2019-02-15
Packaged: 2019-08-06 07:17:53
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 19,560
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16383746
Author URL: https://archiveofourown.org/users/saltyhunter/pseuds/saltyhunter
Summary: CEO Dean Winchester has an unhealthy obsession with Castiel Novak the son of his associate. When he starts receiving nudes from Cas he tries to resist the temptation but the boy is such a tease...





	1. Chapter 1

 

 

“So what’s the deal, what are you gonna do about it?”

Castiel stays silent for a while. He has been ranting since an hour about how attractive the boss of his father is. He met him several times at the fancy dinners his family always has to attend but Dean Winchester never gave him more than a quick polite look while Cas’s fascination for him had been taking insane proportion.

Even if Cas knows Meg just recently he feels comfortable enough to tell her about his massive crush.

“I don’t know to be honest; I didn’t think it that far you know. Like he’s hot and all but with the shit ton of people he meets. And let’s not forget, his shit ton of money… I’m quite sure I don’t have what it takes to catch his attention”

Meg suddenly stands up from the bed and looks at him with wide eyes.

“Wait a second are you kidding me??? Castiel fucking Novak!!!” She reaches to smack him in the head. “Have you seen your ass?? Have you seen your fucking gorgeous blue eyes???”

Cas rolls his eyes. “Yeah like Dean Winchester haven’t seen plenty of that already…”

“Well maybe. But he certainly haven’t met you”

Cas frowns not getting her point. Meg lies back on the bed next to him and pokes him jokingly.

“What I mean dumb ass is that it doesn’t matter how many pretty faces he’s seen out there. The way that you are going to get at him is what will make you have him on leash.”

She finishes with a vicious smile and Cas is suddenly totally curious and activated.

“You… think I can do that?”

“Fuck yeah you can! And consider yourself lucky. You have me as a mentor.”

She winks at him and both laugh at her little speech. Then Meg sits up abruptly.

“Give me your phone.”

“What are you going to do?”

From what he knows about Meg, it’s never a good sign to see her excited like that.

“Do you trust me as a master in the domain of seduction or what?”

“Fine Lolita, there you go.” Cas gives her the phone that was in his back pocket.

Meg unlocks it. Of course she knows the password it’s the name of Cass’ favorite gay porn website.

“You told me you had his private phone number right?”

“Yeah I managed to steal it from my dad’s phone. Wait, are you going to call him???”

Suddenly panicking, Cas reaches out to grab the phone from Meg.

“Wow, take it easy sugar! We’re not calling anybody. At least not yet. Take your off your pants.”

“Excuse me??”

He seems literally in shook which provokes one of Meg’s devilish smirks.

“I’m not going to assault you darling. Just going to send a little tease to your Dean-I’m-fucking-hot- Winchester.”

She stands up from the bed holding the phone in Cass’ direction. She clearly had opened the camera.

“Well what are you waiting for?” she says noticing that Cas is still looking at her.

“Are you sure about this?” He asks uncertain.

“When am I never sure of anything Castiel” she replies rolling her eyes

“I don’t know… it’s just… I’ve never contacted him before and…”

“Shut up. Pants off.  Now.” She cuts him off.  “Stop over thinking this baby boy. We’re just gonna have a little fun. He doesn’t need to know that it’s you.”

“Fine.” Castiel says then stands up to start unbuttoning his pants. He stops, hesitating, looking at Meg.

“Are you being serious? I’m making you shy now?”

Castiel sighs frustrated but a little bit amused.

“At least one of us is enjoying the actual situation.” He groans.

“Believe me sweetheart you’ll be enjoying it to once Mr. Winchester sends you back a nice pic of his hard cock.”

“Sure. Like that’s ever going to happen. He'll more likely just block the number” Castiel says in what seems a completely unbothered voice but Meg can tell by the blush of his cheeks that he is so concerned about this.

 

“Then we’ll just try on a different number duh... Now are you going to get undressed before the apocalypse?”

Castiel just hold his breath and closes his eyes for just a second as he gets off his pants. Meg lets out an appreciative sound.

“You naughty little boy were you wearing those for me?” Meg says eyeing the pink little panties with lace that Castiel is wearing. They’re seductively showing the shape of his huge member.

“I’m wearing them for… hum… practice.” He tries not to look away from Meg’s significant look.

“That so?”

“Should I take off the shirt too?” Cas asks before lying awkwardly in the middle of the bed

“Do you want to?” Meg’s little smirk doesn’t go unnoticed.

“I mean, since we are taking the time to do his, it will be better if we do it properly. That’s all.”

“I hope you know it’s unnecessary to give me a speech if you want to get naked for that sexy boss”

“I don’t want to…”

“Would you mind trying to look a little sexy here?” She approaches the bed to get a better visual of Cas via the phone’s camera.

Meg tries hard not to laugh at her best friend’s embarrassment.

“What do you want me to do now? I’m lying on the bed as you asked.”

“You just look too casual. Like think about how you would be laying if it was Dean in front of you and not my gorgeous face.”

At the mention of dean’s name Castiel’s expression changes immediatly going from annoyed to slightly excited.

“Yeah that’s more like it.” Megan encourages as Cas changed his position.

The click of the camera echoes in the room as she takes several pictures.

“You’re not taking my face, are you?”

“Of course not. Wouldn’t be that much fun if we ruined the surprised for him from the start.”

Meg pauses to look at the pictures she took but doesn’t look satisfied.

“Something’s wrong?” Cas asks her.

“Hmm this isn’t quite the effect I want. Even if I zoom that’s still not it.”

“Do you want me to stand up instead?”

“No you do nothing. But me on the other hand…”

She doesn’t finish her sentence and walks towards the bed and Castiel suddenly looks horrified.

“What the hell?”

Meg takes off her shoes before standing on the bed above Cas, smiling like the devil.

“Why do I feel like you’re taking advantage of this situation?” Cas sighs, resigned.

Meg laughs going back to the camera again.

“Alright! Gimme some sexy shit sweet boy”

 

 

They end up taking more than a hundred pictures in just a few minutes and by the end of it Cas is way too excited and way too hard. Meg has been telling him all kind of dirty stuff involving Dean Winchester fucking him in his office to get him in the “mood for the poses” as she said.

He’s back in his pants now and they’re both lying on the bed trying to pick which pictures they’re going to send to Dean.

“Okay now is the moment for me to ask, are you sure you wanna do this? Tho I highly recommend that you do it.”

“Look who’s having doubts now.” Cas grins mockingly.

‘Well I’m taking that as a big yes then! You do the honors.”

She gives him the phone and Cas looks at the three pictures one more time before sending them to Dean’s contact.

“Now what?” Cas asks. His tone seems platonic but his heart is actually beating so fast that he’s worried for a second he might have an attack. What the fuck did he just do? That was stupid. Stupid. Stupid!!!

“Stop freaking out Clarence.”

He looks immediately at Meg who is now standing and seems ready to leave.

“I can tell from your expression that you’re actually losing your shit. It’s going to be fine, trust me.”

“You’re right. I’m just... hum… You’re leaving?”

“Yep. Crowley is going to find a way to be more of an asshole if I’m late for work. Besides you have things to take care of.”

She eyes his boner suggestively before sending a flying kiss and walking out the room.

Cas sighs heavily and lies back on the bed. His dad isn’t back from work yet which means that Dean is probably still there even if it’s past 10pm. And there’s no guarantee that he will be answering tonight anyways. He decides to go take a shower and of course takes care of his boner while he’s thinking about a certain man in a fancy suit, fucking him in his office.

**Notes for the Chapter:**

> Next chapter is going to be in Dean's POV :) Let me know what you think about the beginning and if you're here from my instagram page.


	2. Chapter 2

 

 Dean looks at the pictures frowning slightly. They’re quite nice but he doesn’t know the number. Normally when he receives nudes they’re always from people he fucked before. Not one night stands but people with whom the sex was very good and he kept their number for whenever he’s up for it.

If someone has this number, technically he’s supposed to have met them before. Though for now he decides to ignore the pics and send a brief message.

“From who?”

Leaving his phone on the bed, he starts getting undressed to go take a shower. It’s past midnight and he just came back from work. His head is literally about to explode and he just can’t to finally get some rest.

 

It has been happening to him for quite a while now and Dean has given up on finding a rational explanation to it. But whenever he’s alone and not surrounded by a mountain of work or boring people who want to take advantage of his money, he always finds himself thinking about Castiel Novak.

Castiel is the son of Bobby Singer’s wife from her precedent marriage.

Dean had known Bobby since he was fresh graduated from college and couldn’t find a damn job with his diploma. He was the first one willing to give Dean a chance even if he didn’t have any recommendations. 

He worked for Bobby for a few years before he left to start his own business. And during this time the old man had become some sort of a paternal figure to Dean and he looked up to him a lot. He still does.

It’s the reason why he feels guilty for having dirty thoughts about Castiel. When Bobby got married earlier this year, Dean was very happy for him. Because he knew how alone he felt since his first wife died.

But as soon as Dean laid eyes on the bride’s son, all he could think about was banging the shit out of those mesmerizing blue eyes. And it just grew worst as months passed to the point that each session of him jerking off was to thought of the boy – still in high school for God’s sake.

It isn’t really healthy for him to keep doing that, but those fantasizes about Cas are the only thing capable of making all the stress from work disappear.

Dean stays in the shower until the water become cold enough to make him want to get out.

He has a half boner, obviously from thinking about Castiel that much, but isn’t in the mood to take care of it right now. He walks in his bed room a towel around his waist and is heading towards the dressing when the sound of a new message from his phone stops him.

He immediately think about the nudes he received earlier and instead of getting some clothes he decides to go check if the message is an answer from the unknown number. He reads the reply while sitting on the bed.

“A little boy in need of a daddy.”

Dean scoffs. What is this? He’s certainly not going to play this kind of game with someone who won’t even tell their name. That could be a set up for all he knows.

“There’s plenty of websites for that. I’m not interested.”

The bulb indicating that the person is writing shows up as soon as the message is delivered. Dean smirks thinking that they must be very ready to get to him.

“If you knew who it was I’m sure you’d be more than interested.”

That catches Dean’s attention. Just a little though, because they could still be lying.

“Why don’t you tell me then?”

“Because it’s more fun like this”

“Not for me. I like to know who I’m talking to.”

“If you keep texting me you might actually guess my identity within a short time.”

“So I do know you”

“We’ve been seeing each other a lot yes.”

“From work or mutual friends?”

“Kinda both…”

“That’s not really helping.”

“If you want to know something you’ll have to earn it Dean ;)”

He smiles a little. Whoever it is they’re very audacious and he likes it. Completely forgetting the idea of putting some clothes on, he lies on the bed.

“What do you want?”

This time the answer doesn’t come right away and he’s a little annoyed by the idea of looking like a high school girl waiting for a text back from her boyfriend.

He’s about to decide to finally go put some clothes on when the new message arrives.

“I want you to come for me.”

Dean’s eyebrow raise. He kinda likes the turn that this conversation is taking. But he still doesn’t want to sound interested.

“Well I’m not so sure about that”

“I am. I know you’d come for that ass.”

There’s a picture attached below the message. It’s this pretty ass again. Bending over his butt cheeks partially exposed by the tiny pink panties.

Dean exhales slowly. In fact this is more than a nice view, it’s very hot and suddenly the image of a certain boy with blue eyes shows up in his mind. Damn it! This is being ridiculous he needs to control that or he’s going to lose his shit.

He considers not answering and going to sleep because he really need to rest but thinking about Castiel had turn him on and the ass he’s looking at on the screen of his phone makes him wanna burry his dick far inside of it.

“Without the panties.”

Dean sends the message then changes his position in bed. He takes off the towel throwing it on the floor. Then sits up completely naked, back pressed against the headboard.

A new picture appears on the screen and Dean takes a sharp breath as he’s looking at the perfect pink hole.

Biting his lips, his hand reaches to start stroking his boner slowly as the other holding the phone continue texting.

“I get that you don’t wanna give me your name yet but if we’re going to do this tell me how you want me to call you”

He waits for the answer, eyes closed, still moving up and down his member. He’s not even surprised when he sees Cas again in his head. He imagines that cute little fuck looking at him with pleading eyes while he fingers his ass…

Dean fist tightens around his now full hard cock and he starts thrusting a little faster.

“Cas…” A deep moan escapes from his mouth.

The sound of a new message makes him snap out of fantasizing and he goes back to a slow pace as he read it.

“You’re daddy. You decide.”

Dean doesn’t even hesitate.

“Cas”

“Ok daddy :) What do you want me to do?”

Dean smiles ironically.

“I thought you were supposed to make me come. Figure it out.”

 

 

**Castiel’s POV**

Completely naked and totally hard on his bed Castiel inhales deeply when he reads Dean’s message. “Figure it out”. Well he’s obviously testing him to see if he’s about that life. And lucky for Cas he is way too excited to chicken out now.

“You wanna face time? We won’t show our faces just what we’re doing.”

If Dean actually accepts to do this Cas is going to see his dick. He is going to see him masturbate and even come in live… Fuck!

His phone vibrates and he checks the new message.

“Deal”

 

The Face Time begins and none of them say anything. Cas almost chokes on his own breath noticing Dean’s hand around his cock. He’s even bigger than what he was expecting and he can’t help but think about what he would feel like to have it inside his tight hole.

With that delicious thought Cas reaches for the Vaseline putting some on his fingers before reaching for his entrance. He can see that Dean is till masturbating and he keeps his eyes on him while sliding a finger in his entrance. Thrusting slowly, Cas closes his eyes a little and imagines that big cock of Dean riding him without mercy.

Hearing Dean making all kind of sexy sounds, he opens his eyes again to look at the screen of his phone. Dean’s fist is going really fast on his erection, his hips moving at the same rhythm.

This view is way too overwhelming for Castiel. Biting his lips he adds a second finger. This time, it’s Dean’s pink lips that he’s thinking about and how they would suck his hole really good. Dean would torture him with his tongue first. All around the soft skin of his ass, kissing and biting without ever giving to him what he’d want. And Cas would curse and whine. Then suddenly Dean would widen his butt cheeks with his strong mainly hands and then burry hiss face in his ass sucking deeply, with rage like his life depended on it. and Castiel would be a mess panting, and begging for more, screaming his name.

“Fuck, fuck!”

Castiel lets out a desperate moan, moving his fingers faster. Dean sounds like he’s losing it too on the phone. Both of them letting out sounds of pure pleasure and excitement.

 Cas makes sure that the way he’s holding the phone shows perfectly what’s going on between his legs. He wants Dean to see all of it. How much of a fucking mess he is for him. When he adds the third finger, he knows he’s not going to be able to keep going for much longer and the hand holding the phone starts shaking. His eyes are closed, whispering incoherent sentences but Dean is present in all of them. He tries really hard to stay as quiet as possible because he can’t risk for Dean to recognize his voice.

But at this point he doesn’t even care that much anymore. All he wants to do is come, now. Now.

“Yes, yes, yes…” He whispers frantically, his hips thrusting in the air, needing a friction, badly. He is so hard hat it hurts but he can’t come yet. Not like this. He needs a goddamn friction, he needs...

“Fuck! Dean--fffuck”

 He lets down the phone and grips his member roughly moving his hand as fast as he’s hitting this sweet little spot in his hole. Then suddenly it happens. All his body shivers violently and he comes all over his stomach mouth open in a silent scream.

 

 

 

 

**Notes for the Chapter:**

> To be honest i'm not proud of the smut in this one. Please let me know what you think.


	3. Chapter 3

 

Dean Winchester waves his secretary as he walks through the hall.

“A package came for you this morning I put it on your desk” she announces.

“Thanks Jo, anything else?”

“Ruby just called, she wanted to know if you still haven’t change your mind”

“Oh for God’s sakes next time she calls tell her to fuck off.” Dean groans annoyed, still walking.  “Actually you know what? I’ll tell her personally.”

Dean enters in his office closing the door a little louder than necessary. He’s quite in a mood that’s for sure. Though the little session he had with that (for now) unknown person shouldn’t have make him that angry. He had the orgasm he wanted and it was really fucking awesome. Like on a scale of 1 to 10 it was mind blowing. But of course he had to imagine his voice! He actually heard Castiel’s voice so clearly that he is seriously considering going to a psy.

He sits down behind his desk and notices the package. It’s a nice rectangular little black box sealed with a red ribbon. It’s kinda fancy look alike and Dean wonders who is trying to get a favor from him. He unpacks it, lifts up the top and suddenly froze. For literally three seconds he does nothing at all but fixing what’s in the box. Then slowly, he reaches to take out the pink panties. The lingerie is very soft against his fingers and looking at it takes him back to what happened last night or preferably earlier this morning.

He closes his eyes hearing the soft moans coming from the phone. He perfectly remembers the sounds of desperation, urge and excitement. All those emotions made him want to fuck the shit out of “Cas.”

He is so caught in the memory that he feels a boner in his pants. The ringtone of the phone on his desk puts an end to it. He opens his eyes abruptly, puts the panties back in the box and closes it before answering.

“What is it Jo?”

“Ruby is on the phone again, you said you’d talk to her personally?”

Dean sighs in frustration. She is really not going to give up.

“Fine, I’ll take her.”

A few seconds later Ruby’s voice speaks in his ears.

“Why are you avoiding me?”

“It ever occurred to you that, I don’t know, maybe I don’t like you?

Dean is annoyed to hear Ruby laugh while he is not even joking.

“I thought we were beyond that since you stole my boyfriend when we were in college.”

“And now you’re finally marrying him. What do you want? If it’s about your stupid bachelorette party, for the last time, I’m not going. Some of us actually work.”

“I can’t believe that the time you were actually fun really existed. Maybe I imagined it?”

The sarcasm in her voice is clear and Dean is already done with this conversation.

“I’m going to hang up now.”

“Okay. Amara says hi by the way.”

Dean almost chokes on his breath when he hears the name.

“Come again?”

Ruby chuckles, happy with the bomb she just dropped on him.

 “She’s back just for that bachelorette party you’re declining. And no I’m not going to tell you in what hotel she’s staying. Guess you’ll just have to come if you want to see her, oops. See you tomorrow bye.

“Ruby, I swear if you’re lying..."

The line goes dead and Dean lets out a frustrated sound.

“Son of a Bitch!”

He hasn’t seen Amara in years and just the thought of her makes him shiver. Ruby really caught him off guard on that one. Fuck! And now he’s obligated to go to that stupid party because there’s no way he is going to miss a chance to see Amara.

 

His phone buzzes in his pocket and he takes it out to check the new message. It’s from “Cas.”

 Instinctively he looks at the box in front of him. Seems like he will have some nice things to jerk off to at the end of the day.

“Did daddy appreciate my gift?

“Would’ve been better if the ass was with it

“Hmm… do you always talk dirty like that when you’re at work?”

“Why don’t you come here and find out?”

“I’d rather have you somewhere I can scream without worrying that other people may hear us while you fuck me good”

A certain part of Dean’s body reacts immediately to the last message. And it takes him a lot of effort not to slide a hand down his crotch. As much as he’s dying to do this right now he got work to do and he loves making money way more than getting laid and that’s not even a lie.

Besides he’s getting really bored by the fact that he can’t know who he’s talking to.

Then suddenly, he has an idea.

“You might never have that chance anyways.  I just got a better offer. So we’re done.”

“Lol. What’s better than me?”

Dean types, hoping that his message is going to force “Cas” to come out from wherever he’s hiding.

“The best sex I ever had in my life just came back in town. And we’re seeing each other tomorrow. So yeah as I said we’re done here.”

Then he turns off his phone and finally starts to work.

 

 

**Castiel’s POV**

 

 

“What are you doing here?”

Megs shouts to be heard despite the noise of the loud music playing in the bar. Castiel is surprised that he actually made to the counter without suffocating from all the people surrounding him everywhere.

“You didn’t show up in school today and I absolutely need to talk you”

“You couldn’t text me? I’m quite busy right now as you can see.” She gestures towards the several drinks she’s making.

“I’ve been calling you a thousand times actually!” Castiel barks then regret immediately being such an ass. He is abusing this recent friendship by coming here at Meg’s work and disturbing her with his personal drama.

“Oh boy you seem pretty upset.” Meg notices, giving him a worried look.

“It’s just…” Cas sighs, frustrated. “It’s Dean.”

“What about him. The pictures didn’t work?”

Cas looks at her with pleading eyes and something in his expression makes her realize that he’s really hurt.

“Can we talk somewhere quiet for just five minutes? Please?”

She nods then turns to another barman nearby.

“Hey, Kevin sweetheart! I have to go pee, hold in for me while I’m gone.”

“You owe me one!” the Asian boy shouts back.

“Follow me” Meg says getting out behind the counter.

She walks towards a door with a “Staff Only” warning on it. And they get inside what looks like the place where people get changed before work and where they stock the cleaning stuffs.

“Alright Clarence, you can spill the tea now.” Meg faces him, that worried look still on her face.

 “In fact the pictures worked more than I’d never imagine” Castiel says taking the phone in his pocket. “But just look...”

He hands it towards her showing the conversation he had with Dean.

As Meg read the little sex chat they had after the nudes her expression turns devilish.

“Damn! You really went for it, didn’t you? Can’t say I’m not proud”

She looks up to wink at him and Cas blushes.

“So are you gonna tell me what happened in that face time or what...”

Cas looks down on the floor but not from embarrassment he just tries to hide his smile from Meg but of course she notices it anyway.

“You naughty little boy! What did you do?”

Castiel meets her wide eyes and smiles big.

“I may have fingered myself... a little.”

Meg’s mouth nearly drops to the floor.

“Oh my… you little fuck!”

Cas chuckles

“Wait did he… you know…?”

She moves her fist up and down in a suggestive way and Cas nods.

She smirks. “So how big was he?”

Cas’s teeth slowly bite his lips when he whispers : “Very big.”

Meg whistles.

“At least one of us had a fun night.”

Cas’s face suddenly saddens.

“Yeah that was before he decided that he was done with me”

“You’re kidding right?”

“Scroll down to the messages of this morning”

She does and her eyes go wide while reading the texts.

“What a bitch!”

Cas sighs sadly then reaches to take back his phone.

“I don’t know what I did wrong. Maybe I went too far by sending him those panties.”

Meg seems to think about it for a few seconds then immediately shakes her head.

“Nah I think he’s just way too excited over that pussy.”

“And It’s not like I can exactly compete with “the best sex he ever had”

“Don’t let him get to your ego my boy, you’re a total snack and this dick doesn’t know what he’s missing.”

“Well I know what I’m missing”

Suddenly the door behind him opens and they turn to see a man not looking happy at all.

“There you are!”

Castiel notices immediately the panic from Meg’s expression.

“Oh my God. Crowley I’m sorry we were just leaving.”

“I don’t wanna hear your excuses. Get your ass back to work. Now!”

He snaps and Cas frowns.

“It was all my fault you don’t need to blame her.”

“It won’t happen again” Meg says quickly. “C’mon Cas time to go.” She grabs his arm and almost drag him out of the room.

“He doesn’t seem very nice!” Castiel shouts once they’re back in the wild atmosphere.

“Yeah, Crowley has that effect on people!”

Castiel has the feeling that there’s more to it than that but he doesn’t have the time to pursue on that thought as Meg gets behind the counter to continue doing her job. He hopes that she won’t get in any trouble because of him. It was stupid to come here and waist her time, stupid to keep thinking about a grown ass man who doesn’t give a fuck about him. But for some reason Castiel can’t find it in him to give up on Dean Winchester. He needs to get that man.

 


	4. Chapter 4

Castiel walks toward the door ready to leave for school even if all he wanted to do this morning was to stay in bed and cries his eyes out. Sadly, seeing Meg last night at the club didn’t do much to make him feel better. He came back home feeling as shitty as he had been all day.

Being rejected by someone like Dean Winchester is clearly not going to be easy to forget. And his insomnia is a perfect proof of that. He stayed up for the most part of the night thinking over and over again about a way to fix this mess. Though on the other hand, he has his pride after all and he doesn’t want to keep pinning after Dean for the rest of his high school life. After all there are a bunch of hotties out there. But the thing is that Cas isn’t the best when it comes to “people skills.” Hell he’s even lucky to have someone like Meg being friend with him.

When he opens the door, she is right there, standing in front of him.

 “Hey there, sweet boy!” She greets him cheerfully. “How’s it going?”

Cas almost sighs of relief. That familiar face is a figure of comfort and he could really use some of that right now.

“I’ve been better as you can… imagine” He shrugs, closing the door behind him. “I hope your boss didn’t go too hard on you after I left last night” he adds with an apology in his eyes but Meg just laughs it off.

“Don’t you worry about that. You think a big girl like me can’t handle a little bit of trouble?” She takes a few steps towards him invading his personal space and Cas just roll his eyes already feeling better from his sad mood this morning.

“Sure you can. Now quit stealing my oxygen.”

She winks at him then turn around to walk towards her bike parked in front of the house that Cas only notices now.

“I thought you came here for me to drive you to school. And where’s your bag by the way?”

Getting on her motorcycle she takes the helmet and throws it towards Castiel who catches it just in time before it hits him in the face.

“Today I’m saving you from eight hours of boredom and suicidal thoughts.” She seems amused by the fact that Cas looks absolutely terrified.

“Nope. No way. This is not happening Meg. I’ll take my car thank you.”

“I figured you’d say that, good luck on finding your keys though.” She adds with a smirk.

Checking his pocket Castiel sooner realizes the horrifying truth and start doing this thing with his face where he’s trying to look angry but just end up looking like an adorable little fuck.

“Give them back. NOW.” He walks towards her palms open, an unhappy look on his face.

“C’mon Clarence, you’re a big boy now. Stop being such a pussy and get on this thing. It’s going not to eat you.”

“Considering that I’m actually mad at all the pussies in the world you shouldn’t be mentioning them to try making me do something that obviously scares the crap out of me.”

“Are you also mad at mine?” She asks using a fake innocent voice. Trying to fight back a smile Castiel crosses his arms.

“I am going to be if I don’t get my keys back.”

“Hell, I can’t wait to see how my pussy is going to react to an angry Cas!”

She bursts out in laughter seeing Cas’s face turn violently red and is about to talk again but he stops her immediately.

“Alright, enough! Please, just shut up. I’m coming with you, you won.”

She continues laughing as Castiel put on the helmet and gets behind her.

“Just so you know if I end up in hospital today, it’s all on you.”

Starting the engine she turns her head slightly to the back.

“You might want to wrap your arms around me for more safety” she warns him a devilish smile.

 

Castiel fears for his life during the entire ride. But at least while he was focus at all the cars that almost hit them on the road, he wasn’t thinking about Dean Winchester and the pain of being rejected was gone.

Thankfully the ride isn’t long enough to make Cas feel nauseous but nonetheless when he finally gets on his feet he almost kisses the ground.

“You okay there?” Getting off the bike Meg eyes him with an ironic look that only pisses him off.

“I think I’ll survive thanks.”

“Great! Cause if you die now I’m not going to be able to waste your money.”

“What?”

She points a finger at the building behind him and he turns in that direction.

“We’re going to do some shopping sweet boy!”

“This is Victoria’s Secret.” He says blankly.

“Isn’t that where you got your panties from?”

Oh Crap! Evil Meg is back and Cas knows that he’s so screwed if he goes in there with her.

“Remind me why are we doing this again?”

“Because your little heart is broken and I can’t put up with you being all depressive and shit.”

“So you’re basically doing this for you.”

She turns her back at him and start walking towards the entrance.

“Well I’ll be inside! When you’re ready to have some fun, just come find me.”

Cas can basically hear the smile in her voice.

 

**Dean’s POV**

Ruby was stupid enough to think that Dean wouldn’t discover which hotel Amara is staying at. A man like him has plenty of resources to know those kinds of things. But even if he has that information now, he decides to wait until the bachelorette party tonight to finally see her.

“We also have this model in three more different colors” says the lady in uniform.

Dean considers taking the lingerie in red for a second then he remembers that Amara’s favorite color is black.

“This one’s fine” he replies.

He’s been at Victoria’s Secret for about half an hour getting some juicy things that he’s planning to send at Amara’s hotel room. From the days when they were still “a thing” he remembers how excited she always got whenever Dean bought her sexy stuff to wear.

The lady who’s helping Dean out is saying something about new arrivals of other similar models but he isn’t listening anymore. Someone just caught his attention and he’s having a hard time believing his eyes. Castiel Novak, here. This is not a hallucination. And he’s not alone. There’s a girl with him.

Dean doesn’t even bother trying to think rationally before he acts. Taking his credit card from his wallet he hands it to the lady...

“I think I’ve got all I need. Can you check those for me while I’m making an important call?”

“Of course, Mr. Winchester.”

She walks away and Dean immediately follows the direction where he saw Castiel disappear with the girl.

He notices them quickly. They’re both laughing as the girl is holding a bra in front of Castiel’s chest and for some reason Dean feels suddenly pissed. Who the fuck is she? As he approaches, he tries to think about the rare possible ways for him to not look stupid for whatever he’s about to do and doesn’t come up with nothing much.

This is not right. Going to talk to Cas is a very bad idea. Besides what is he even going to say? Hey buddy, you mind telling who’s that chick? I don’t like the thought of her hanging out with you because I’m a fucking pervert who’s obsessed with everything about your goddamn body.

Yeah that pretty sums up the whole situation. But for now it isn’t helping.

“Hello, Castiel.” They turn around at the sound of his voice and it takes him a lot of self control to remain calm when he sees Cas’s face. It would be quit awkward to be having a boner right now.

“Dean?” The incredulous look on his face could’ve been almost hilarious if Dean was being able to calm down. He doesn’t even know what he is upset about at this point.

“Shouldn’t you be in school?”

“Yeah… hum… uh…” Of course he can’t come up with an explanation and it makes Dean even angrier.

“School was dismissed today.”

 He keeps fixing Cas’s eyes before turning reluctantly his attention to the girl who just spoke.

“I’m not sure we have met before.” The smile on Dean’s face couldn’t have been more fake.

“I’m Cas’s girlfriend.”

She puts her hand around Castiel’s waist and Dean looks back at his face to see him blush.

“And I suppose Bobby doesn’t know you skip school to come buy lingerie with your girlfriend.”  
He expects Cas to be highly uncomfortable at the mention of his father’s name but on the contrary he notices something cold in his eyes and so is his voice when he finally speaks.

“As Meg already said, school was dismissed and with all due respect I think that the rest of it is none of your concern.”

“I’m afraid that it is” Dean replies calmly. “Considering the fact that before your parents took their flight for Tokyo this morning Bobby asked me personally to keep an eye on you.”

That couldn’t be more far away from the truth. Bobby travels all the time for business and loves taking his wife with him. They have enough trust in Castiel to leave him all alone for a few days. However his lie has the effect expected and Castiel looks uncertain now.

“He didn’t say anything to me.”

“Well I’m saying it to you now.”

“And you made your point.” Then he smiles fondly to the girl. “Let’s continue shopping Meg.”

Before Cas can turn his back to him Dean grabs his arm firmly.

“No I don’t think so.” Cas’s eyes widen and during a moment being so close to him makes Dean forget how to breathe properly.

“Hey! What do you think you’re doing?” Again, this annoying girl.

“Castiel and I need to have a little chat concerning his behavior when his father is absent.” Dean says still looking into Cas’s eyes, who seems to be debating on how he should react to Dean grabbing him like that.

He doesn’t wait for Cas to make a move or say anything before dragging him as he starts walking away.

“Let me go.” Cas whispers angrily, visibly in fear of not wanting to make scene.

Dean totally ignores him and goes to take his belongings from the lady who helped him do the shopping.

“Have a nice day Mr. Winchester.” She says while handing to him the Victoria’s Secret shopping bags and his credit card. Castiel stays quiet besides him but Dean can sense the tension in his body and as soon as they are outside Cas tries more furiously to get rid of Dean who is still pissed as fuck and seeing red.

“It’s okay, I got the message. I’m going to school now. Just let me go!” Cas stops whining when they stop in front of luxurious Audi. A man in suit is standing there and takes the bags out of Dean’s hand to go put them in the trunk before getting on the driver side.

“I’m not going anywhere with you.”

Dean reaches to open the backseat door, and then finally get his hand of Castiel’s arm.

 “It’s up to you but keep in my mind that I can still call your father and tell him about your little escapade.”

“I wasn’t doing anything wrong!” Cas pleads, his big blue eyes glowing in anger. And Dean instantly feels all the blood in his body going down to a specific part of his anatomy.

“Good luck trying to convince him that you had a good reason not to go to school.”

Castiel doesn’t answer and looks at him with a very furious look before finally getting in the car. Dean lets out a brief victory smile before getting in after him.

“Let’s go Arthur.” He says to his chauffeur who simply nods then the car starts and enters the traffic.

Dean refuses to mentally start freaking about what he’s going to do with the boy right now. This whole thing is crazy but if someone can handle crazy it’s him.

“Where are you taking me?” Castiel asks somewhat resigned.

“I haven’t decided yet.”

**Notes for the Chapter:**

> Where do you think Dean is taking Cas???


	5. Chapter 5

They’re in the car for a few minutes already when Cas decides to take his phone out of his pocket and have a little word with his outrageously bad friend.

“I can’t believe you just stood there and watched him take me away!!!”

The answer comes immediately.

“Are you for real now??? it’s not like you showed any sign that you were against it and btw I did try to help you “boyfriend.”

Cas gives a side look towards the man sitting on the other side of the car. Dean is currently in the phone and doesn’t sound happy about whatever it is he’s talking about.

“I’m mad at you for the next century.”

“I got you some time with Mr. Giant cock. You're welcome.”

Cas almost choke reading the message but lets out a little smile. He can’t deny that he’s in fact grateful for that.

“How’s it going by the way?”

“Actually, he’s on the phone with someone who apparently screwed up their job. And he has a chauffeur. Can you believe THAT???”

“Lol from what you’ve told me he’s a fucking multi millionaire. Clarence guys like that have a dozen cars and don’t even drive half of them.”

Castiel rolls his eyes instinctively this is such a typical Meg thing to say.

“okay now you’re exaggerating.”

“well anyways I’m sure that if he’s not riding his own car he’ll more likely save his energy to ride you.”

“omg Meg! Not now. I’m really trying to stay calm here.”

The car slows down then stops totally. Castiel looks out the window and see the familiar building where his dad works. He then turns towards Dean, who just finished his call, a confused look on his face.

“What are we doing here?” he’s trying not to find the impassible look on Dean’s face hot as fuck. The man is just looking at him, nothing special here, but Cas’s hormones don’t agree.

“Since you decided that school wasn’t worth your time today…”

“It was dismissed” Cas says interrupting him then regrets it by the cold glance that he gets.

“Do NOT cut me off when I’m talking.”

The tone is harsh, the order clear and for a few seconds there’s a battle going on in the way they intensively stare at each other. Cas can only hope that he doesn’t look like he’s about to pass out because he’s holding his breath. Then he capitulates the authority coming out from Dean’s expression being too much to handle.

“I’m… I’m sorry” he says quietly and Dean’s face doesn’t soften as he continues where he left off.

“I was saying that we are going to use this amount of time you have to waste in an educative way, with you being my assistant for the next six hours.”

That being said Dean gets out of the car and then speak to his chauffeur.

“You already know what to do about the packages in the trunk; I want you back here by 4pm.”

“Yes, sir.” The man replies ad Cas notices a British accent.

“You’re coming or what?”

Cas looks down at the conversation he’s having with Meg and types quickly.

“I think I’m going to hell.”

Then he slides it back in his pocket, takes a deep breath and opens the door.

 

Castiel came at Winchester & Co a couple of times but now it just feels different, walking behind the boss as his unofficial puppet. Cas is perfectly aware that something about this situation should’ve bothered him at least a little though he just can’t be upset when on the other hand he’ll get to see Dean Winchester bossing people around. And he might also be one of those people. Something about that makes Cas shivers from excitation. Seeing Dean in a “boss mode” is a sight of him that his hormones will probably enjoy.

“Are you even listening?” Cas stumbles upon a hard chest and takes immediately a few steps back meeting the gaze of a very pissed off Dean Winchester.

“I’m sorry Dean.” It’s already the second time that he’s apologizing to him and they didn’t even spent half an hour together!

“Okay first of all, today it’s going to be Mr. Winchester. I’m not your dad’s friend, I’m your boss. So you keep that in mind ‘cause I hate repeating myself.”

Cas nods, he can’t talk for now, not yet. There’s just too much going on at the same time. And Dean standing there in this gorgeous suit sculpted for his body is one of them. Dean looks so gorgeous that he feels terribly inferior in his blue jeans and random shirt. And his self confidence is suffering a lot from that. He needs to find a way to remain calm and not looking like a terrified deer facing its death.

The intense aura coming from Dean Winchester is just such a turn on that he doesn’t know how to react. If only he was like Meg he would’ve known the right thing to say or to do. How to fight back or how to flirt or looking like a bad ass. But it isn’t in his nature. In fact the only time he felt somewhat a little bit of power was the first time he texted Dean.

“And second thing, what did I just say?”

“That I shouldn’t call you by your first na…”

“No I mean before that! When you were so stuck up in the clouds you didn’t pay attention to what’s in front of you.”

“Oh… hum... uh”

Dean takes a few steps in his direction eyeing him intensively which make Cas wanna curl up in a corner to hide.

“I have a meeting in a few minutes. Take notes”

Cas knows that he should answer otherwise this is going to get awkward really fast but he still remain silent. He forgot his bag on Meg’s motorcycle and don’t have things to take notes. He should be saying that to Dean instead of thinking it.

“Did you hear it this time or do I have to say it again?”

“I don’t have anything to take no—

He doesn’t finish his sentence, Dean is already walking away.

“Ask Jo!” he just shouts without looking back.

As soon as Dean isn’t invading his personal space Cas sighs from relief. He notices Jo from where he’s standing but before going to her takes his phone out of his pocket.

There are two unread messages from Meg.

“Lol, have fun in hell.”

“Come back to me in one piece tho.”

He types quickly.

“HELP”

“omg Clarence what is he doing to you? Do I need to come quick his ass?”

He smiles slightly shaking his head.

“Chill Meg it isn’t like that. He’s just treating me like crap and I could really use your skills right now.”

“Well I’m glad you ASKED!!!”

 

**Dean’s POV**

 

This concept is boring and so are the people presenting it to Dean. They must really think that he’s an idiot if they believe that he’s going to invest in that bunch of crap.

There are three men. The nerd one is talking about technical stuffs that make no sense to him and the two others seem to be having doubts about their expectations for this meeting. Then there’s Jo of course and then Castiel, who’s frowning slightly while writing down things in a block note.

For some reasons he seems to have really been paying attention the presentation. And Dean is curious to see what he’s been noting this whole time and that gives him an idea. There’s no obligation to continue to endure the torture of this meeting anyways and besides it’s wasting his time.

“That’s a no.” When Dean speaks the nerd goes suddenly silent and the atmosphere changes radically becoming tenser. Then one of the two other men, the one that has been introduced as the chef speaks immediately.

“Mr. Winchester we are willing to…”

“My assistant here thinks that this partnership between us is a bad idea” he says designating Castiel. “Please, explain these gentlemen why...”

Dean smiles interiorly. He shouldn’t be enjoying putting Cas under projectors that much but even if it’s childish he likes seeing him embarrassed.

He expects Cas to mutter some incoherent words, blush and run out of the room but to his surprise, when he speaks looking at the three men, he seems perfectly calm.

“There’s a flaw in your budget. According to your explanations you except to have a benefit incompatible to the amount of merchandise you should’ve had in stock to begin with…”

“We are actually working on more...”

“I wasn’t finished” Castiel cuts the nerd off

“Also, your concept doesn’t match Winchester & Co’s policy at all. We are very concern about our image and this… well there’s no proper way to say that so this unprofessional box of mess isn’t gonna do it.”

He shrugs, kind of a sorry-not-sorry look on his face and Dean is so struck that he almost applauds. The men desperately turn to Dean a latest light of hope on their face. He is the boss after all and they must think that whatever his assistant’s opinion is on a business project he is certainly not going to consider it but unfortunately Dean agrees with Castiel. They need to go home work on their thing much more or going to present it to someone dumb enough to take it.

“We’re done here.” Dean says standing and buttoning his vest. “My secretary will show you the way out.”

And with that he just leaves Castiel following behind him.

“So what was it back there?” Dean asks turning his face towards Cas who seems now slightly embarrassed.

“Just basic math. It was kind of obvious.”

“Yeah well, good job. Now go get me some coffee.”

“Excuse me?”

Dean stops walking and turns to see that Cass is not moving either.

“What, do you have ear problems?”

“No I perfectly heard that but last time I checked you had two feet and I’m not your pet. This isn’t even a real job.”

There’s a brief moment of cold silence following that speech during which Dean debates the pros and the cons of fucking Cas right there in the hallway. Then he just smiles.

“You know what? I think I’ll take it black.”

 

Dean is back in his office for quite a while now and is typing on his computer when his phone buzzes in his pocket. Normally he wouldn’t pay attention to it but nothing about what he’s doing today is normal. So he checks his phone.

He is surprised to discover a message from “Cas.” He thought that this person had given up since the last time they texted.

 “Every time you boss me around, I’m having a hard time not to get on my knees and suck your big cock.”

Wait, what? No, this can’t be implying what he thinks its implying.

Dean fixes his phone for an undetermined amount of time and it’s in that position that Cas finds him when he enters the office almost a few seconds later.

“Black as you asked.”

 

Castiel poses the coffee on his desk and then look up to meet Dean’s eyes.

They stare at each other for a moment. Dean trying to read him because he can’t really jump in conclusion so damn fast. If he’s wrong about this, things can get very bad. But what he’s actually seeing in Cas’s expression gives him the confirmation that he needed then he slowly gets up and goes lock the door.

When he turns back to Cas, he can see that he knows that dean knows and that he certainly expects what’s going to happen next.

“Well what are you waiting for? You said you’d drop on your knees.”

 

For the first time Dean notices a cocky smile on Cas’ face and he can’t deny the effect that it has on him.

Cas walks towards him without breaking eye contact until they’re close enough to breathe each other’s air.

None of them speak because honestly no words are needed here and Dean decides to let Cas take the lead of whatever is going to happen next.

Lightly, he feels Cas’s hands on his waist, one of them slowly get down to the front of his crotch and pressing his palm against his erection. It’s getting harder to look at Cas’s fake innocent expression without leaning to kiss his so tentative lips but Dean just stay there letting him do what he wants, for now.

Cas’s hand start rubbing softly Dean’s hard penis under the thin fabric of the pants, Dean wishes there was no fabric at all and then Cas presses his fingers harder against him and he takes a sharp breath to restrain the moan in his throat.

“I need you to tell me what you want Dean.” Cas whispers.

“You already know what I want.” Dean replies eyes almost closed his face showing a mixture of emotions between pain and pleasure.

“Say it.”

Cas’s hand rubs harder on Dean’s erection creating, a delicious friction that sends flames in Dean’s lower belly. He is now biting his lips to help him stay quiet.

“Your mouth...” Dean says with a tormented voice, “I want your mouth, now.”

And it seems to be all that Cas needed because he immediately start unbuttoning Dean’s pants sliding it down his legs with his underwear.

Dean’s breathe itches. Every nerve in his body is READY for what’s going to happen. If only Cas could stop being such a tease and get it done already. He is so hard and having Cas standing so close looking at his dick like he’s about to give him the best head of his life doesn’t help at all…

 “The thing Mr. Winchester is that…” Castiel looks at him and his cocky smile is back, wider this time. “As my temporary boss, you don’t pay me enough for that kind of task.”

He takes a few steps back leaving Dean shook and looking likes he’s about to explode. “I quit.”

And it’s the last thing he says before walking out the office closing promptly the door behind him.

Dean lets out a frustrated groan.

“Son of a bitch!”

 

 

**Notes for the Chapter:**

> What's going to be Dean's next move??? Comment below :)


	6. Chapter 6

**Notes for the Chapter:**

> If you made it that far I guess it's time I tell you that this fanfic is from a prompt that I posted on my instagram account : @destielprompts.  
> You can go follow it, there's a lot of ideas to inspire you write your own destiel fiction. (see picture below, the fan arts used aren't mine.)

                                                                               

                                                            

 

 Meg sits up from the bed a shocked look on her face.

“You did WHAT?!”

 She screams so loud that Castiel instinctively cover his ears.

“Jesus Meg! You’re gonna break the windows!”

 “Are you out of your mind?” She continues, lowering her voice this time and laying back next to Cas.

“I’m not sure I understand the reason behind your surprise.”

“Oh! sweet boy…” she sighs dramatically. “From what I saw of your Dean Winchester this morning, leaving him with the blues balls like that may not have been your brightest idea.”

She uses that tone to make Cas understand how badly he screwed up but he refuses to take the blame.

“Wait, hold on. You’re the one who told me in the first place...” Noticing where he’s going Meg interrupts him before he can finish.

“What I told you Clarence, is that you could give a little tease, just to make him go nuts while he’s working but this…” She laughs while Cas finds none of this situation funny at all. “Oh boy this will make him go wild after your ass!!!”

“Alright, enough of this!” The pillow he’s resting on is thrown at Meg’s head when she continues laughing which now makes him have serious doubts about something he was so proud to have done. “Stop, you’re freaking me out!” Cas groans miserably rolling on his back, eyes now fix to the ceiling until Meg’s face appears on top of him.

“This is all your fault.” He’s pouting in such a cute way that she has trouble not to smile at him.

“No, but I do get why you’re upset. You had a chance to get that dick and you let it go away!”

“Your hair is assaulting my face.”

Meg chuckles then shift position to place herself completely on top of him.

“He probably hates me now.”

“How can anybody ever hate you Castiel” She replies with a smirk.

“Because I’m a bad boy?”

“Well, daddies do love their boys being bad once in a while don’t they?”

Cas pouty face disappears to let out a bit of a smile  when he suddenly notice that there’s something wrong with how Meg is kneeling over him, his body caged between her legs. And the expression on her face could’ve warned him about what devilish plan was on her mind if he wasn’t so distracted by the thought of Dean fucking Winchester.

“Meg no, wait!”

“TICKLES!!!” She yells before attacking him. Of course it’s too late now to escape and Cas sooner finds himself barking of laughter and begging for mercy at the same time. If his phone haven’t started to ring at this moment she would’ve probably continue until he peed himself.

Breathless, they both turn their gaze at the phone on the night stand table.

“You think it’s him?” Cas asks quietly.

“Only one way to find out.” She lets go of him then reach to take it, looking at the contact name appearing on the screen.

“Ugh it’s your dad” she scoffs throwing it at Cas. “Be sure to tell him that I’m still not sucking your dick while he’s gone. He keeps thinking that we’re dating.”

Rolling his eyes at his annoying pervert friend Cas answers the call.

“Hey dad.”

“The house isn’t in ashes yet?” an affectionate grumpy voice says on the other line.

“With how strong your hope is that this will happen, I’m sure it isn’t so far anymore.”

Bobby chuckles and Cas nods at Meg gesturing that she’s going to get something to eat before she leaves the room.

“Listen uh, there’s some social duty I need you to fill for your old man since I can’t attend it.”

Cas doesn’t even need to know what it’s about  to already annoyed.

“Seriously dad, what now?”

“No need to go all “teenage wrath” on me, it’s nothing too formal. Let’s say a simple celebration event.

“With all your business freaks? I think I’ll pass.”

“Well, I do take note of your complaint but I wasn’t asking. You’re going, end of discussion. It’s tonight, I’ll send you the address.

“I hate this.” Cas sighs defeated.

“Your mom says hi. Oh and if you’re with that girl Meg…”

“Dad we are NOT dating.” He cuts him immediately trying to prevent what he’s about to say next but of course it fails.

“Anyways you already know the rules: not in our bedroom, and use protec…”

“Bye dad.”

Castiel hangs up and let his body falls back heavily on the bed.

The door opens and Meg appears. Holding an opened pack of chips between her teeth, two canned drinks, and several drunk food in both hands. Cas sends her a meaningful look.

“Did you really have to take out the entire fridge up here?”

“Fuck you” she mumbles before dropping it all on the bed.

She sits and pick a chocolate bar then notices how Cas is fixing her.

“What, you’re suddenly in love with me?”

When he finally speaks he smile so intensively that she worries about his sanity.

“I’m taking you out tonight.”

Meg blinks then puts down the chocolate she was about to take a bite in.

“Should I be worried? Is it the part where I tell you that this friendship has always been platonic to me?

He laughs.

“Well I still love dicks but it’s good to know.”

 

 

Castiel can’t decide what annoys him the most. The fact that he doesn’t recognize most of the people in there or the vicious look that men have been sending in their direction ever since they got here because of course Meg decided to choose the most provocative dress that she could find when they went shopping after he received his dad’s call.

“Wow, this isn’t how exactly I’ve imagined a “boring” event with “boring” people to be.”

“Trust me I don’t understand either.” Cas says ignoring Meg’s sarcasm.

Even if his dad told him that it wasn’t going to be too formal Cas wasn’t excepting it to be basically a party.

“Maybe you got the address wrong?

“Yeah, very funny.”

But in fact Cas is somewhat having the feeling that something about this isn’t right. He recognizes some of the people here for sure but he has absolutely no idea of what’s going on, if anything special was happening he’s certain that he’s dad would’ve tell him about when they talked.

Then suddenly Adam, the son of one of his dad’s relatives stumbles upon them. From how he’s having trouble standing Cas can tell that he’s far beyond drunk.

 

“Hey man, what are we celebrating here exactly?”

“You know what I honestly don’t care.” Meg says next to him. “I’m going to get a drink.”

She walks away and Adam whistles, obviously looking at her ass until Cas snaps a finger in front of his face to send him back to reality.

“What’s the party for?” He asks again.

“Ruby’s getting married!” Adam shouts even if the music isn’t that loud considering the band playing is out there in the back yard and that they’re currently inside the house. “And of course she decided to brag about it.”

“Who?”

“You don’t even know who that is?” He starts laughing hysterically to the point Cas begins to worry that he might puke on the floor right here in front of him. “Who cares anyway? Just enjoy the food and…” He stops mid sentence his gaze finding Meg again. “I was going to say enjoy the girls but I see that you already got yourself some pretty masterpiece over there.

“Oh no she’s not… we’re just friend.”

“Really? Then you won’t mind if I go introduce myself to her?”

“Yeah you can…”

“Cool man, see ya.” He goes quickly in Meg’s direction and Cas can’t help but roll his eyes.

“…do that.”

Adam is undoubtedly the type of guy who thinks they’re so attractive that no girl can resist them. Poor bastard, Meg is going to eat him alive.

 

**Dean’s POV**

This day has officially gone to shit. Dean looks angrily at his reflection in the mirror, readjusting his tie. He was just in the phone with Amara’s hotel reception, getting the awful news that she was taken to the hospital this afternoon due to food poisoning. Which also means that the cold revenge plan he programmed for Cas is ruined now. And that fucking sucks because the only reason why he called Bobby and lured him into making Castiel come here, was to make sure that this arrogant bastard would see him with Amara and realize that he was nothing more than a random temporary distraction.

Though, it seems like he’ll more likely just go home and have a long private session of masturbation. There’s no point in staying much longer and looking dumb trying to avoid Castiel once he’ll get here. He washes his hands, dries them then walks toward the bathroom door to open it and find himself in front of Castiel Novak.

Dean reads the surprise in his eyes and see him recover from it quickly as he’s about to walk away.

“Not so fast, I’m afraid.”

A firm hand pressed on  his forearm Dean drags Cas inside, closes the door and pushing him back against it.

“You know I gotta admit it was a very good performance this morning.”

“I’m glad you appreciated it.” Cas grins ironically.

Dean smirks, deciding it’s better to play a little instead of getting angry. Then he raises a hand toward Cas’s face, letting his fingers slide softly along his cheek, his thumb running around his mouth. They remain silent a few seconds, face close to each other, Cas’s breathe apparently disturbed judging by how his chest is raising fast.

“My plans for you tonight were going in a complete opposite direction but I think I just changed my mind.”

“Me being here has something to do with you?”

“Oh come on, don’t tell me you didn’t see it coming. Is that what you usually do, being a little fuck, tease people around and then leave before things get serious?”

“I have no problem with “things getting serious” as you said. But you being an asshole is a little bit of a turn off.”

His expression is so arrogant right now that Dean almost sees himself in the young boy. Leaning closer, his lips only inches apart from Cas’s,  one hand is still cupping his face while the other slides down along his chest to finally rest on his erection that he presses lightly.

“We both know that’s not true.”

“I don’t care what you think; I’m done talking to you.” Cas turns immediately his back ready to open the door but Dean knows better and pushes his body against his in order to keep him caged between his torso and the wooden material. There’s absolutely no possible way for Cas to escape now.

Dean then leans toward Cas’s face turned on the left side, not looking happy at all but also not looking like he isn’t somehow enjoying the contact of Dean’s erection on his ass.

“Going somewhere?”

“Don’t think for a second that you have me trapped I can always scream.”

“Oh I’m sure as hell going to make you scream.” Following his words his hands unbutton Cas’s pants giving him space enough to pull out his hard cock. He’s amused to see Cas doing so much effort to act indifferent when he can literally see how red his face has already turned from excitation and feel how tensed are every muscle of his body.

Dean tightens his fist around Cas and appreciate the sensation of it pulsing under his palm. Drops of sweat are now running down Castiel’s forehead and cheeks. He’s panting but still not capitulating and it’s what Dean wants, he want Cas to give up all the control to him. After all isn’t that what Cas was after since the beginning when he texted him?

“You know this could’ve gone differently if you haven’t been such bad boy boy.”

Dean whispers to his ear, moving his hips forward to create a friction of his crotch and Cas’s ass.

He groans frustrated, his face so red that Dean chuckles a little. He will have no mercy. Cas needs to learn that he owes him some respect. His ego still suffers from being humiliated by some high school kid.

“You said something?” Dean says seeing that Cas is trying to mutter some incoherent words.

A smirk on his lips he lowers his face to put a kiss on Cas’s cheek letting the contact last as he finally move his fingers, creating little circle on the tip with the same torturing pace that the other hand start jerking him off, up and down, up and down, pauses. Up… down.

“Go to hell...” Cas manages to say

“Not if I can’t bring you there with me” Dean replies sarcastically. “And that’s exactly what I’m planning to do.”

“I’m not going to beg… hmm” a deep moan escape from his throat when Dean squeezes his hands a bit massaging his  balls at the same time.

“I’m sorry, you were saying?” Dean mutters close to his lips.

“Fffuck… fuck you!”  Cas closes his eyes, breathless and  visibly trying to restrain himself from moaning so badly.

 And then it happens. Just like that, suavely. Their lips melt together, like they were meant to be and this simple gesture produces such an amount of torment inside Dean’s chest that he suddenly can’t seem to have enough of this contact. His lips move feverishly all over Cas’s mouth deposing little kisses, sucking a on the bottom, biting the corner close  to his chin, then sliding up again to kiss Cas deeply, their tongues caressing each other with a consuming passion. It feels warm and wet and so good, so good that Dean groans desperately, so good that he’s rocking his hips harder against Cas’s ass, so fucking good that all he can think about is having Cas jump on his dick right here and right now.

“Cas…”

“Dean…”

They moan each other’s name, pulling apart just enough to get some air before connecting again, sucking, biting, exploring. And it’s certainly because all these emotions feel as overwhelming to Cas as they’re to Dean that he finally explodes screaming desperately:

“Fuck me Dean! Please, now. Fuck me!”

He’s panting against Dean’s lips, who now slows down to a much gentle rhythm, kissing all over his cheeks, his forehead, and ears trying to calm him down as he’s having trouble to stay still.

“Shhh, shhh, it’s okay Cas”

He puts a smooth kiss on his nose, “it’s okay”  gives a small on his bottom lip. “I’m gonna make you feel better baby.”

Both of his hands around Cas’s dick move faster now, thrusting vividly against the skin. He tortured Cas long enough he can let him have what he wants now.

“Dean, Dean, Dean…”

Cas mutters over and over again eyes closed and body resting completely against Dean. If he wasn’t pinning him he’d be lying on the floor now.

Moving his hand as fast as he can Dean continues to kiss Cas all over his face. He can’t keep himself from doing it now that he’s tested how great it feels to give this type of affection to Cas.

 “Feels good uh?”

“God yeah, fuck... oh Dean, I think I’m...”

“No not yet.” Dean stops him, slowing down the pace of his thrust.

Cas suddenly open his eyes to look at Dean, desperate, angry and needy.

“Turn around” Dean commends. Confused and way too excited, Cas still obeys without questioning it.

 Then Dean drops on his  knees and Castiel literally hold his breath.

Taking Cas back in his hands Dean leans in, but doesn’t take him all in his mouth at first and just gives little kisses on his tip, sucking a little there, driving Cas crazy, squirming, panting and sweating mess. Then Dean puts him out of his misery and swallows him entirely and makes a gagging noise when it reaches his throat and he notices exactly how Cas react to the sound of him choking on his dick.

It’s as if the roles were reversed and it that it is Cas now being the daddy who punishes the bad little boy. Cas’s hand reaches behind Dean’s neck digging his fingers into  his skin as he holds him still to start thrusting inside Dean mouth, fucking his way frantically inside the sweet, wet, warm cocoon.

Dean just stay there and take it all, eyeing Cas under his lashes, enjoying to see him finally lose control and totally abandoning himself. The most beautiful thing he ever saw, such a fucking turn on. Then out of nowhere the thought that he could get used to this crosses his mind. He could get used to having Cas so hot for him all the time, he could get used to Cas being all his and that’s exactly what he’s thinking about when he feels the warm liquid inside his mouth and swallows it all without hesitation.

 

**Notes for the Chapter:**

> I have a massive headache by the time i'm updating this, I've been writing since 4am I hope the result is good enough for you guys!


	7. Chapter 7

**Notes for the Chapter:**

> Happy Halloween!!! And thanks for continuing to read this story even if half the time I think it's not good...

Castiel finishes readjusting himself, consciously avoiding Dean’s gaze in the mirror. He’s blushing way too much and feel beyond embarrassed  to endure his macho behavior.

“I’m taking you back home.”

“That’s very sweet but I don’t need you to do that.”

Cas briefly meets his eyes and notices that Dean’s cocky expression has been replaced by frustration which makes him feel a lot more better. He loves the idea that he has already enough power over Dean Winchester to know exactly how to upset him.

“I’m not leaving my car here” he clarifies. “I barely know these people.”

“That’s not a problem. I can get it back at your house by tomorrow morning.”

Having nothing else to fix on his clothes and no more excuses to keep avoiding the face-to-face Castiel finally turns toward him.

“I don’t need a babysitter.”

 “I’m not saying you do.”

“Great, have a good night.” He’s already walking to the door but Dean steps right in front him and with the way he looks at Cas, he wonders for a moment if they’re going to have a second round.

“This rebel act you’re trying to pull up is not going to work. Not when you basically begged me to be your daddy.”

Blushing even harder, Cas looks down before recovering quickly then exhale.

“Look, I really appreciate what happened earlier…”

“Appreciate huh?” Dean cuts him, eyebrow raised, making Cas roll his eyes.

“Fine it was perfect, volcanic, mind blowing! Is that good enough for your ego?”

“Hmm… I think that’ll do it. Now if you’re done giving me lame excuses I think it’s time we get the hell out of here.”

“I was about to tell you that I didn’t come alone.”

He finally admits, regretting it as soon as he sees the look on Dean’s face. Well it’s not like he could’ve just go and leave Meg behind. What kind of fried would he be? But that’s the thing, they lied to Dean about the nature of their relationship and Cas did enjoy that back at Victoria’s Secret but now a few hours later he wishes it never happened.

“I’m guessing you brought your girlfriend?”

There’s no good answer to that. If he tells the truth he’ll have to explain why he pretended to date Meg in the first place and that is not an option.

 “Go find her, I don’t mind having one more passenger.” Dean exits the bathroom without giving him the time to reply and just as the door closes behind him, he feels a vibration in his pocket. Checking his phone, he discovers a message from Meg.

“Are you going to be very mad if I leave with that handsome ass who just gave me two orgasms in a row?”

“I think we’re equals, since Dean insists on taking me back home. P.S. He just sucked my dick”

“FUCK!!! You should’ve done a sex tape wth?”

Cas laughs shaking his head.

“You too lol”

Now he’ll have to say to Dean that his “girlfriend” left earlier because of an emergency.

_________________

 

 

Saying that it isn’t a fun ride back at Castiel’s would be the understatement of the century.

None of them speak and he can basically smell the hostility coming out from Dean, though he doesn’t make any effort to break the silence. After all it’s not like Dean and he could ever be something like “a couple.”  Even if Cas he’s hot for him, he’s still realistic, this thing they have going on between them isn’t gonna last, hell he’d be surprised if they last tomorrow considering how pissed Dean obviously is right now.

“You might as well, turn the radio on if you’re gonna be an ass for the rest of the ride.” Cas finally says.

Dean doesn’t even look at him, eyes still fixed on the road.

“Alright, keep acting like the very mature grown up man that you are.”

That gets a reaction out of him.

“Oh I’m sure it’s very mature to let other men suck your dick while your girlfriend is downstairs.”

Cas fights back a smile, he actually can’t believe that Dean is being jealous and the hell if he’s not going to use that against him!

“Why do you even care?”

“I don’t, I just pity her.”

“Well don’t. Trust me, Meg isn’t the type of girl to need people to back her up. Besides, she’s very open minded.” He adds not wanting to look like a total bastard in front Dean, even if he’s not certain that he’s in position to lecture him about how to treat girls well.

“What do you mean she’s open minded is she gonna sit there and watch while another man has his dick up your ass?”

“In fact, this already happened. So mind your goddamn business and stay out of my relationship.”

It’s the biggest lie Castiel probably ever told in his whole life  but he doesn’t even blink. The adrenaline of getting Dean Winchester angrier by the minute is pulsing through his veins making it impossible to have control over his mouth.

The cold silence falls back inside the car and Castiel reaches to turn the radio on.

 

 

He doesn’t realize that he’s fallen asleep until a hand on his shoulder wakes him up. The door on his side is open and Dean is leaning over him. Confused by the decor surrounding him, he frowns slightly at Dean.

“Wait, what are doing here? This is not my home.”

“No but it is mine, and before you can get started on a drama about how you’re not going to get out of the car, I’m tired and way not in the mood to keep sitting behind a wheel.”

“Of course.” Cas mutters not buying Dean’s bullshit. And he wonders how far enough he will have to push him to finally get the reaction he wants.

He unbuckles the seat belt and Dean takes a step back to let him out. He closes the door then turns to face Dean with defiance in his eyes.

“Now, what?”

Dean grips him firmly by the collar then pushes him brutally against the car.

“Now I do what I should’ve done since this goddamn morning.”

That being said he leans to Cass’s face and there’s nothing soft about the kiss they exchange. It’s a battle of pure savage manly testosterone,  in which Dean wants to show Cas who’s the boss here, in every sense of the word.

“Turn around.” They finally break apart to catch their breath and Cas looks at him confused.

“What, you’re afraid someone might see?”

Dean probably lives in the most quiet and unproblematic neighborhood plus his property is very vast but when Cas execute this order it isn’t for none of the reasons above. It’s because it’s exciting and Dean being all bossy with him might make him come undone. Hell the lust he spotted in Dean’s eyes clearly told him that this was a moment he was never going to forget.

He doesn’t even realize that Dean is unbuttoning his pants, for the second time this night, until it reaches the ground. The chill air creating goosebumps on his naked legs and another kind of sensation where Dean puts his hand around .

“Bend over.”

Castiel does as he’s told and is now resting on the hood of Dean’s luxurious car.

He can basically feel how much Dean needs this and that he’s taking the time to prep him just so that he might not hurt him. But Cas doesn’t need to be prep he’s been ready for Dean since day one, when he saw him at this wedding.

“If you’re not going to fuck me now, I’d rather not freeze my balls. Thanks.”  He still manages to sound somewhat cocky despite the fact that he is a complete ball of nerves and that Dean would just have to hit the right spot to make him explode.

Then Cas hears Dean getting out of his pants too behind him and a second later his hands are resting on Cas’s hips.

“You’ll have it as you wish.”

And that’s the last thing Dean says before putting his erection against Cas’s entrance, pushing slightly inside of him. Cas winces a little at the invasion and Dean takes it easy until he’s far enough to start thrusting at a slow pace.

Waves of pleasure already start pounding in Cas’s veins every time Dean goes a little far away. He doesn’t even try to move though he couldn’t have even if he wanted to because of how firm Dean’s grip is on him.

Each thrust seems like a punishment, harder and deeper, kind of like Dean knew that it was what Cas was craving for all this time he was testing his nerves during the car ride.

Dean’s sharp rhythm, becomes wilder creating obscene noises of his skin hitting Cas’s ass who’s biting his lips to restrain himself from disturbing the peaceful night.

It’s really happening, now, his biggest fantasize : being fucked by Dean Winchester. And he won’t certainly be able to walk tomorrow but he doesn’t fucking care.

__________________

 

“So what do you wanna do after school?”

It’s already the morning after and Cas is exhausted, and sore in some parts of his body he wasn’t even aware existed until now. He yawns, raising his head toward Dean sitting against the headboard.

“What kind of question is that?”

“The kind of question I want the answer to?”

Cas frowns, eyeing him suspiciously.

“You know we don’t actually have to do that thing where you pretend that you’re not using me just for the sex.”

Dean suddenly gets out of bed perfectly naked and Cas have a hard time keeping the eye contact.

“See that’s the thing with you. You’re so fucking contradictive. Blaming me because I act like an asshole but when I try to behave you make fun of me.”

“Is this our first marital dispute?”

“Okay, forget I said anything.”

Cas laughs and Dean eyes him angrily.

“You’re just so easy to upset, I can’t help it.” Ignoring him, Dean heads toward the bathroom and Cas sigh heavily.“Fine, get back here and I’ll answer.”

He stops walking then turn around reluctantly, still somewhat angry and Cas can’t help but find it absolutely adorable. Dean gets back in the bed and lies over Cas’s legs, who lets out a victorious smile.

“I want to be a lawyer.”

“Why a lawyer?” For some reason he seems to be very interested in the answer and Castiel just shrug.

“I don’t know to be honest. I guess I’m just attracted by court or maybe I just watched too much episodes of “How to Get Away With Murder.”

“Of course you would watch that shit.”

Castiel looks so offended that Dean almost tears up from laughing which makes him angrier.

“Connor is very hot, and now that I think about it I’m pretty sure he’s the college version of you.”

“And he can burn in hell for all I care.” Dean says when he’s finally calm.

There’s a moment of comfortable silence during which Cas  just watch  him play randomly with the sheets and suddenly he begins to be afraid of the feeling invading his chest. He can’t allow this to happen because he knows that there’s nothing good coming out of it.

“My little brother wanted to be a lawyer too.”

Something in Dean’s voice warns Castiel that this isn’t a happy subject.

“What happened?”

Dean sighs and rolls on his back to lay on the mattress, eyes fixing the ceiling, clearly lost in unhappy thoughts.

“I think the fact that we had to grow up without a paternal figure made him feel like he had to seek protection somewhere else and that’s how he got involve in deep shit with the wrong people.”

Castiel waits for him to say more but when he doesn’t he finally asks :

“How’s he doing now?”

“He’s in prison. ‘Been six years now, has one more to take in.”

 Dean gets out of bed, clear sign that the conversation is over but before he can get in the bathroom Cas’s voice make him stop.

“You’re not responsible of what happen to your brother, he made terrible decisions that lead hi there.”

He doesn’t turn to look at Castiel but the pain in his voice is obvious when he speak again.

“I should’ve looked out after him. It was my goddamn job.”

 

__________________

 

Castiel eventually regains his house and spend the day texting Meg about every single details of the night he just had. She never replies and he thinks that she might be having the weekend of her life with Adam.

Though he would’ve never thought that he was her type, but he hasn’t been friend with her long enough to know what exactly her type of men is. In fact coming to think about it he realizes that there’s so much about her that he doesn’t know, including where she lives.

 Somehow Meg always managed to never say a lot or change the subject when it came to her and Cas never pushed it far because he guessed that she would talk about it whenever she felt like it.

And when he sees her at school on Monday he doesn’t understand at first that she’s in a bad mood and keep asking her about her week-end until she finally snaps.

“Yes I’m fine, just leave me alone Cas!”

She starts walking away after slamming violently the door of her locker. Taken aback by her attitude, Cas stands there in shook before starting to run after her and grab her shoulder when he’s close enough.

That’s when he notices the bruises on her skin, going down her neck. They’re in a bad shape of purple and only hidden because of her hair.

“What’s that?” He steps in front of Meg holding her arms firmly and she yells trying to escape from his grip.

“Get out of my way!”

“Not until you tell me what’s going on!” He snaps back.

She continues to fight to get rid of Castiel’s hands until she breaks down and start crying.

Heartbroken to see his best friend like tha,t he instantly pulls her close against his chest, tears forming in his own eyes.

“Whoever did this to you, they’re going to pay.”

**Notes for the Chapter:**

> What do you guys expect for the next chapter? Please let me know, comments make me happy:)))


	8. Chapter 8

**Notes for the Chapter:**

> I apologize in advance for any type of mistakes you're going to find. I re-read myself but i'm in a rush right now. I'll come back later for a third reading.

 “Was it Adam?”

It’s the fourth time that Castiel asks the same question and Meg exhales deeply.

“You seriously think that I would’ve let that skeleton-like play boy beat the hell out of me?”

“Then who? Why are you not telling me?”

Meg frowns and on her face it looks she’s about to castrate  Castiel. She has been avoiding him all day until the break time where he basically forced her to sit down and talk about the subject that she obviously didn’t want to.

“Because you can’t help, okay?!” She notices that Castiel looks pained by her tone and tries to remain calm. “This whole fucking mess is entirely my fault anyways I could’ve avoid it.”

“How can you be responsible for this?” He asks incredulously, already opening his mouth again to harass her on giving the name of the bastard who caused the bruises on her body.

“Look Castiel, I get it. You’re my friend and you’re worried about me. I do understand that and I’m grateful  to have you trying to look out for me but there’s just things that you should let me handle on my own. I’m fine, this situation is temporary.”

Castiel frowns looking torn between continuing to argue with Meg and not pushing her too far . He sighs choosing the second option.

“And how long exactly is temporary?”

“Temporary.”

Cas gives her a severe look and Meg could’ve almost smile if this whole situation didn’t suck that much.

“Seriously, I’ll… I’ll take care of it okay?” Castiel doesn’t even look slightly convinced so she puts her best “fake smile” on.

“I promise.”

“Yeah…”

But he already has a plan in mind.

 

 

 

 

**Dean’s POV**

“So you were just going to ignore me and let me there to die ugh?”

Amara walks in Dean’s office looking gorgeous as if she didn’t spend the week-end hospitalized due to food intoxication.

“I sent you flowers.” Dean looks at her briefly before going back to his computer.

He wasn’t excepting that Amara would be out so soon and to be honest he didn’t even think about her, his mind preoccupied by someone else…

“Of course you did. You’re such a gentleman Mr. Winchester.”

She approaches Dean’s chair and forces him to take his attention out of the screen.

“Well I did appreciate the gifts you sent me before this unfortunate accident.” When Dean looks at her again, she’s wearing nothing but an assortment of lingerie and the trench coat she had on when she came in, is laying on the floor.

“Right…”

He’s about to take a decision about whether or not he should let Amara have what she came for when the door of his office suddenly opens.

“There’s a fucking door. You knock on it damn it!” Dean looks like he’s about to fire whoever just came in until he discovers that the intruder is none other than Castiel.

“Cas I’ll…” He pauses visibly unsure about the right thing to say for just a few seconds while Amara looks extremely annoyed by the interruption. “I’ll call you back.”

 “No. I want to talk to you now.”

Cas has this expression that get Dean weak every time. The one where he looks determined to have what he wants despite having to kick the devil in the ass.

“And who’s that now?” Amara asks suspiciously, turning to face Dean again.

“Amara, I think we should probably do this later.”

He stands up , takes the trench coat from the floor and put it back on her.

“What if I don’t want to do this later…” She leans closer to Dean’s face her lips almost touching his and fingers wandering along his chest going down to the front of his pants before his hands stop her.

“We’ll have more privacy later ‘Mara.”

“I think he’s asking you to leave.”

That was Cas, sounding very impatient and slightly angry, causing Dean to smile ironically while Amara face him with her darkest expression.

“What are you his translator?”

“No actually I’m the guy he’s currently fucking but yeah, I guess I can also be a translator once in a while.” Eyebrow raised she turns back to Dean, smiling a little.

“You never disappoint do you? Always playing on both team.” That’s the last thing she says before exchanging a deep kiss with him and walking pass Castiel, a victorious smile on her lips.

“Jealousy looks very cute on you” Dean says once they’re finally alone.

“I didn’t come for that.”

“Then for what?”

“I need your help.

Dean leaned on his desk a cocky smile on the corner of his lips.

“I’m all years.”

“ I think one of my friends might be in trouble.”

“What kind of troubles?”

“I saw bruises on her body like… Like she has been beaten up.”

Dean shrugs, unbothered.

“If it’s that serious, you should probably go to the police.”

Cas gives him the _“are you seriously that dumb?”_ look which make Dean roll his eyes.

“ Okay, you obviously don’t want to go the police. So what?”

“I was wondering if maybe you could… have someone to follow her and…”

“And?”

He sighs visibly having trouble finishing his sentence because he came to the realization that it’s ridiculous but say it anyway.

“I don’t know. The person would just  make sure that she’s okay when she gets home or something.”

“And if she’s not, burst out in the room, gun in  hands and fire everybody to rescue the damsel in distress?”

“Why did I think it was great idea to come talking to you?” Castiel is about to head out when Dean speaks behind him.

“You were expecting me to jump in excitement at the idea of having  to babysit your girlfriend?”

Cas immediately stop walking and turns to face Dean a shocked expression on his face.

“I didn’t… how did you…”

“Look I’m gonna put someone on it but do not expect that I will tell my employee to interfere in people’s private life and do whatever it is you’re used to see on TV, you understand?”

 

 

**Castiel’s POV**

But Castiel couldn’t just sit his ass and wait for someone to solve his friend’s problems. So after class instead of heading home, he decides to follow Meg.

It’s not easy for Cas to keep track of her bike with all the traffics and he almost lose her at a certain point but the idea of his best friend being in danger was enough to give the motivation necessary.

After a certain distance the circulation become more fluid and he barely encounter a car as he arrives in a neighborhood that isn’t nearly as chic as his. And just by the look of it, he could tell that this couldn’t be a safe area for Meg to live in.

He parks his car at reasonable distance that would prevent him from being noticed by Meg and his eyes followed her as she entered one of the buildings.

He decides to stay there, not knowing what to do else. Following Meg seemed to be a bright idea at first but now that he’s here, he realizes that if Meg has a problem at home he won’t be able to help from the car.

Sighing he reaches for his phone and types a message to her.

“Hey, just checking in. Let me know if there’s anything wrong please.”

And with that he just waits.

________________________

 

 

It’s 9pm and Castiel’s stomach keeps reminding him that he needs to eat something. But for some reason he couldn’t bring himself to get out of the car to go search for somewhere to grab a snack.

He’s considering it for the third time when he notices a familiar face getting out of a car on the other side of the street. The lack of light out there doesn’t help him identify the man but he’s certain he has seen him somewhere before and when he start walking  toward Meg’s building he finally get a good look at his face.

“Crowley?”

As soon as he recognizes the man, a bad feeling invades Castiel’s chest and he remember his first encounter with Meg’s boss. She seemed to be kinda scared of him too, which somehow had stayed in the back of Cas’s mind.

Without thinking about it twice he gets out of his car and walk inside the building too. He arrives just in time to  see Crowley take the stairs and he does the same, while pretending to look at something on his phone in case Crowley decided to look behind him and remembered his face from when he went to see Meg at the bar.

 They finally get on what seems to be the second floor and Cas stops in front of a door pretending to search for keys in his pocket as Crowley continue walking. His gaze follow to see which room he  was going to enter in.

He could just be living there and Cas would be making a big deal out of nothing but he needed to be sure.

And when Crowley knocks on a door at the end of the hall, Castiel is certain that it’s Meg who’s going to open it but when it did open from where he is he doesn’t see much as Crowley walks in.

Suddenly the door in front of him opens and an old lady appears.

“Oh! Hum… I’m” He’s about to give an excuse like he got the wrong flat or something but the he decides to take the opportunity.

“I’m here to see Meg.”

The old lady eyes him suspiciously and he gives her what he thinks is his cutest smile and she makes a gesture of the head, directing the end of the hall.

“105” she mumbles before going back inside and slamming the door.

“Thank you…”

Cas literally run to the door 105 where Crowley disappeared just a moment ago and knock frenetically on it. While he’s waiting he doesn’t notice anyone talking inside and he just hope that it’s not Crowley who’s going to come to open it.

But No it’s meg and as soon as she lays eyes on him she looks extremely frustrated.

“What the fuck are you doing here?”

“Why did I just saw your boss walk pass this door?”

She quickly gives a worried look behind her before returning his attention to Cas.

“Castiel, go home. I’m serious.”

She’s about to close the door but it opens widely and Crowley appears and Cas instantly hate the man without having a proper reason to. At least not yet but he really feels like he’s about to have that reason.

“Isn’t that your boyfriend?”

Meg looks panicked as he’s about to take a step toward Cas and she runs in front of him, grabbing Cas’s arm in a manner to make him understand that he has to leave.

“He’s going Crowley.  I was telling him to…”

“I’m not going anywhere Meg! If this dude is bothering you, we can go to the police.”

This time it’s horror that is painted on her face when she pushes him violently in the chest, looking like she’s in the verge of crying.

“Get the fuck out of here, you obsessed freak!”

Grabbing her firmly by the arm, Crowley drags her back inside.

“Leave her alone!” Cas yells but before he can get to Meg Crowley takes him by the collar.

“You should’ve minded your own business young boy.”

“Crowley, please! He’s just stupid, he’s going home now!” Meg is crying now and the distress in her voice break Castiel’s heart. He wants to comfort her, promise her that everything is going to be okay and that they’re going to get rid of the bad guy.

But he doesn’t even see the punch coming and suddenly feel a fist connecting his right ear-drum.

He falls unconscious on the ground.

**Notes for the Chapter:**

> It's been two weeks since my last update 'cause I had a writer's block and was looking for a co-writer. Well I didn't find one so i'm going to do as much as I can to continue writing this story because you guys seem to like it :) Thanks for the support.


	9. Chapter 9

Dean doesn’t remember exactly how he got there, but he isn’t surprised that things escalated quickly. Because, whenever he seemed to be around Amara he could never control his urges. Even years without seeing her didn’t change a thing in that. And it’s one the reasons why he let her kiss him in front of Castiel earlier today. That, and the fact that he desperately wanted to prove something to the young boy : he too could be in a relationship with other “women” and the thing they had going on between them wasn’t “that” important.

Yeah, he may have convinced Castiel but he would have to do a lot more better to convince himself.

“Are you even with me?”

Dean looks down to meet her pouty angelic face mixed with a hint of lust in her gaze. Breathe harsh and lips shining with his precome. Seeing her like that brings Dean back to when they were still in college. Those were, somehow, the good old days. Even if he was worried about Sammy who just had gotten in prison he never missed an occasion to forget, at least for a moment, how much of a crappy old brother he was. And expanding his sexual horizon was the only way he found to calm down his grief.

That’s how he didn’t resist too hard when Ruby’s boyfriend started to give him enough hint to make him understand that he was interested. And when they brought Amara in the game, things became even more spicy and the three of them could never have enough of each other, especially Dean and ‘Mara.

“Long day at work, that’s all.”

Dean says moving his fingers through Amara’s hair and guiding her head towards him.

“But you’re going to take my mind off of it, don’t you?”

She smiles cockily before taking Dean in her mouth again.

 

**Castiel’s POV**

It hurts. That’s the first thought that crosses Cas’s mind when wakes up. Then he notices the ceiling. He’s laying down, why is he laying down?

He tries to sit up and realizes that he’s tied up.

“You’re awake.”

His gaze follows the direction of Meg’s voice and he notices her, standing next to the door of the small empty room.

“Meg are you okay?”

He feels a relief seeing that she seems alright. He doesn’t know where he is though he has the feeling that Crowley might be somewhere out there. By the look of it he’s deep trouble but with Meg’s help they’re going to find a way out of this for sure.

“They’re going to kill you Cas.”

There’s a long silence following that and she doesn’t try to break it, apparently giving Castiel the time to process what she just said.

“Excuse me?”

Meg sighs and then walks closer to him and that’s when Cas notices that something had change in her eyes. They don’t look so friendly anymore. That spark of immaturity and craziness had gone and now it’s just cold.

“It’s drug. The night you brought me to that fancy party, I was supposed to make a delivery for Crowley and… Well I thought I would’ve had the time to do it after but then I met Adam and it just…” She pauses and shrugs.

Cas frowns in anger and when he speaks again there’s pure venom in his voice.

“That’s why he beat you, didn’t he? You forgot to do some stupid delivery!”

Meg doesn’t even look slightly overwhelmed to see him caring that much. She keeps eyeing him with a blank expression, her tone still calm despite her harsh words.

“Anyways Cas, you should have just fucking listened to me.”

“Are you being serious? You’re my best friend of course I wasn’t going to listen to you!”

“You don’t know me Castiel.”

And she walks away, leaving Cas paralyzed in stupefaction. This can’t be happening. His Meg wouldn’t let him here to die!

He knows her. He _knows_ her.

 “They’re probably going to overdose you with some shit then dump your body far away.”

And with that, she closes the door behind her.

**Dean’s POV**

It was Arthur on the phone. His chauffeur and also one of the men involved in his business with Crowley. The news that he had for him weren’t good at all. Dean had a hard to believe that Meg could be involved in any kind of things with Crowley but Arthur was clear : the girl that he was charged to keep an eye on left with him.

But that wasn’t even the worst part of it. Arthur recognized the “boy from Victoria’s Secret”. He entered the building too, right after Crowley and he didn’t see him coming out of it.

That smelt like deep shit.

Arthur had follow Crowley’s car and as soon as he gave Dean the address he jumped into some clothes leaving Amara asleep in his bed to go fix this bloody mess.

“I swear Crowley, if you do anything to him…”

The phone call isn’t going well so far and Dean has to use all his self control to keep an eye on the road and not lose his shit with Crowley who doesn’t make it easy at all.

“You’re in no position to give me orders Winchester.” Crowley’s tone is so unpleasant that Den decides to change his. Crowley is a proud son of a bitch and questioning his authority will do him no good right now.

“He’s the son of my associate. I’m sure you understand why I can’t risk anything to happen to him.”

“Sounds more like your problem than mine.”

Dean takes a deep breath and mentally count to five before speaking again.

“He’s just a stupid kid Crowley, that’s it.”

“Well I see you and his girlfriend agree on that.”

Dean immediately thinks that he must be talking about Meg. And it leads both of them to another round of argument in which Dean nearly explodes when he learns that Meg has been working with Crowley.

 “What the hell Crowley! Are you out of your mind? We talked about this. No fucking minors in the business!”

“Meg is family. Her old man owes me money and been MIA for three months now. So she’s paying for him.”

Fucking shit. They aren’t getting anywhere like that and Dean needs to find an agreement with Crowley.

“ What about 10 million, you can have my partnership in New York, but  you let them both go.”

There’s a silence on the line and Dean knows that he’s going to win this one. Because Crowley has always wanted to extend his business to NY. A lot of money to be made there.

“25 million.”

“Crowley…”

“It’s that or nothing.”

That fucking bastard!

“ For starters , I’ll give you ten…”

“Bye, Winchester.”

“No wait, Crowley!”

Damn it!

Dean punches violently the car wheel, seeing red. It’s not about the money, he has plenty of that but he just hate the guy. Really, really hate him.

 “I’ll make the transfer.”

“ Great. And make sure that I don’t catch the boy nowhere near my bar anymore.”

“Just let them go. I’ll take care of the rest.”

 

**Notes for the Chapter:**

> For those of you following me on instagram (@destielprompts) I know I promised I'd bring Sam in this chapter but it didn't seem like the right moment. Maybe in the next one :)


	10. Chapter 10

 “So what’d you do this time to screw up your relationship?

Dean looked at Sam, considering for a while to act as if he didn’t have a clue about what his brother was insinuating but even if he’s good at lying to himself he can’t do the same with Sammy. Dean was pretty sure that his time in prison wouldn’t prevent Sam from seeing through his bullshit. Some things just never change.

“What makes you think I’m the one who screwed up?”

Dean takes an offended tone, trying to make his brother feel guilty for insinuating that his grown ass is still incapable of handling a relationship but Sam laugh it off.

“Well I was just guessing but I was right apparently.”

“You don’t even know what you’re talking about,” Dean groaned rolling his eyes.

“Why don’t you tell me?”

Dean shifted awkwardly in his seat. It’s not like Sammy didn’t already know about all his past kinda fucked up relationships with both men and women but this time was different. Dean always tried to be somehow the paternal figure that Sammy didn’t have the chance to grow up with. How exactly could he manage to tell to his little brother, who basically worshiped him, that he’s been sexually involved with a teenager who just dumped him after discovering (under unfortunate circumstances) his involvement in some drug dealing shit?

“It wasn’t that important.” Dean shrugged but the look on his face sold him out.

“Are you trying to lie to me?” The smirk on Sam’s lips made his brother roll his eyes.

“It was actually by mutual agreement that we decided to end things.”

Dean remained silent and Sam could clearly see that he was trying to keep himself from talking about it, but he wasn’t going to let Dean Chicken out of this. His life here in prison was death-like boring and he could really use some entertainment.

 “Are you going to explain what that means, or will I have to guess?”

Deeply exhaling, Dean finally decided to rip the band aid off. He’s had too much going on his mind lately anyway and if didn’t let a bit of it out he might end up losing his shit… He did lose Castiel after all and was still trying to figure out a way to deal with that.

“So… hum, I’ve been hanging out with this guy for like a week and…” Sam makes a gesture of the head, encouraging him to go on. “He’s like… we…” Dean paused, fighting to find the right words. “I mean, what I’m trying to say is that…”

Sam had never seen Dean being so uncomfortable to talk about the people he dated before and as a concerned look appeared on his face, he leaned forward resting his elbow on the table between them.

“Look Dean, whatever it is you don’t have to feel weird about telling me.” He paused then reached for his brother’s hand across the table. “It’s just me.”

 

**Castiel’s POV**

“Rise and shine Clarence!” A voice way too enthusiastic disturbed the silence in Castiel’s room and suddenly the covers were pulled away from his body breaking the comfortable cocoon of depression.

“Meg… I’m really not in the mood.” His voice came out raw and he made a face at the pain in his throat. After he got tired of crying over Dean-freaking-criminal-and-liar-Winchester he tried to scream his pain away face buried in his pillow but of course it didn’t do him any good. He was relieved when his dad called a few days ago letting him know that they couldn’t come back home yet because of some inconvenient. At least he didn’t have to fake being okay while all he wanted to do was sleep through the next few decades of his life.

“Oh no sweet boy, I’m not taking any of that anymore. You’re gonna move your pretty ass out of this goddamn bed and we’re going to school.”

Cas rose his head a bit, his eyes immediately meeting Meg’s worried ones and he instantly gave up on being rude and unfriendly, she was just looking out for him.

“You Meg Master, actually want to go to school?”

“Or… we can go sabotage “ _his”_ car”.

 Cas fell back on his pillow and the groan he let out made Meg’s heart ache for her best friend. She sighed heavily then sat on the bed next to Cas, running gentle fingers through his hair.

“Hey baby boy. Trust me I know what a broken heart feels like but sooner or later you’ll have to get out there and continue living your life even if it hurts like a son of bitch.”

“I think I’m gonna keep rotting under the covers for a little while then.”

Meg laughed and smacked his head playfully.

“Not under my watch Clarence.”

 

 

 

 

**Dean’s POV**

Dean couldn’t believe that his hands were shaking. Sam would probably laugh at him if he was here though he was the one who suggested that Dean did this.

_C’mon man, it’s not that big of a deal._

Except that it was. It’s been nine days since the last time he saw Castiel and it was when he came to rescue him from Crowley who was gonna kill him because he had the nerves to sneak around his business. Business in which Dean was involved too, goddamn it!

No wonder why Castiel didn’t say a single word on their way back. Dean could still perfectly see those moments clear in his head. After all he spent the past few days relieving them over and over again.

 

**_9 days ago_ **

“I’m sorry Cas, this should have never happened.”

Dean turned slightly toward him and the expression he caught on his face felt like a thousand knives bursting through his chest. Cas was hurt, disappointed, disgust and even horrified, all of that because of Dean’s stupidity.

“Crowley’s not like that usually…” Dean attempted to say before quickly shutting his mouth. What was he doing trying to defend this bastard? Hell he could burn in hell for all he cared!

“You probably want to know how I got involved in business with someone like Crowley…”

“I don’t.”

Dean took a deep breath. This sounded so cold, not like the Cas he knew, not like the Cas he loved…

“In fact, I don’t want to know anything about you anymore.”

Dean kept his eyes fixed on the road during the rest of the ride because he couldn’t find the courage to see on Cass’s face how much he meant what he just said.

Meg’s neighborhood was further than Castiel’s so they got to his house first. Once only the two of them remained in the car, Dean had to fight the urge to ask Meg if Cas would ever forgive him but before he could talk, she spoke from the back seat.

“If you really somewhat care about him, you’d better get the fuck out of his life. Forever dude, you’ve done enough damage.”

And now there he was nine days later, standing in front of Castiel’s door and shaking like a fucking teenager.

 

**Castiel’s POV**

Cas opened the door and literally froze when he discovered the man standing on his porch.

“Dean.”

“Cas.”

They both remained silent for a while, all the unspoken things feeling heavy in the atmosphere between them. For a few seconds Cas had the opportunity to see how devastated Dean was, and mad at himself and sorry about what happened. But the thing that made his heart break even more was the resignation he saw on Dean’s face. And just like that he knew why Dean had come.

“I wanted to make sure you were okay,” Dean said finally. “You didn’t return none of my calls nor reply to my messages.”

_I almost got killed by the man you’re doing drug business with. How the fuck do you expect me to be okay???_

Castiel wanted to scream a lot of things at him. He wanted to punch Dean again and again and then there’s this part of him that wanted to throw his hands around his neck and kiss him so bad because he missed his touch, he missed the feeling of their skin against each other.

“I’m okay.” He said simply, it wasn’t necessary to create a drama. He didn’t have much energy left anyway.

“Good, that’s good.” Dean smiled but it didn’t reach his eyes. When he lift his hand to let it rest on Cas’s shoulder, Castiel felt his throat tighten as he saw Dean trying to repress tears too.

“You didn’t have to come all this way just to do that...”

Castiel almost didn’t recognize his voice when he spoke.

 _“Even if it hurts like a son of a bitch…”_ He heard Meg’s voice say in his head and he felt a single tear run down his cheek.

“I had to,” Dean replied his grip tighter on Cas’s shoulder. He bit his lips, eyes watering despite how much effort he seemed to put on trying not to cry.

They looked at each other, regret filling the air but it had to be done. Cas was a teen and Dean a grown ass man involved in deep shit that could actually put Cas in serious danger and it already did.

They reached for each other’s lips at the same time. And the kiss they shared resumed all the things they couldn’t say out loud: _I love you,_ _I have to let you go, I’m gonna miss you…_

Cas will never be able to say how long the kiss lasted. The only things he was aware of where Dean’s perfume, his hands on his back, the violence of his lips on his, their body pressed against each other as if they were trying to melt to form a unique one… One last kiss in memory of the good old days.

 

 

 

Meg went downstairs to see what the hell took Cass so much time and she froze when she saw him standing all alone, the door still open.

“Hey sweet boy…” she said quietly as if she already knew what happened. From where she was standing she could hear Cas’s sobs, it was easy to guess who was it that knocked earlier.

 

Castiel turned to Meg, giving his best friend a poor smile despite all the tears covering his face.

“He came to say goodbye…” Cas managed to say. Then his knees felt suddenly weak and he almost collapsed on the floor but Meg ran just in time to catch him, pulling him into a hug, her hands circling him like she was holding onto life.

“I got you Clarence… I got you _sweet boy._ “

**Notes for the Chapter:**

> That's it guys. That's the end of this story :( If you've followed me till here a big THANK YOU. Thanks to those of you who came here from my instagram account and to the others who just randomly foun this on AO3. I'll probably start another fic in a few days... And don't forget that this story was based of one of my prompts on my instagram account @destielprompts. See ya next time guysss


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